Dog Boarding in Oakland, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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1. Kyle H.

Rover 101
Over a decade of experience!
Hyde Park, Chicago, IL, 60615
1.9 mi. away
Boarding
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$55
per night

My dog has boarded with Kyle a few times and is always sooo happy to see her. She clearly has a way with dogs. I would recommend her and definitely use her again.

Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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2. Tania B.

Rover 101
Star Sitter
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
4.1 mi. away
Boarding
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$50
per night

I LOVE my new dog sitter Tania! ? So, we did our meet and greet about a month before his actual stay. She was very nice and Cooper liked her too! I decided to book her that day! She kept Cooper the following month and she did everything right! There wasn’t an enormous amount of pictures and videos sent to me but just enough sent for me to know that he was doing good and was safe! That’s all I really needed to know! I would definitely book with her again! She has such a sweet, calming, aura!

Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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3. Makeba L.

Star Sitter
WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
14 reviews
11 repeat clients
from
$47
per night

One of the best experiences I've ever had! Makeba was wonderful and took great care of my fur baby Benny. I absolutely recommend Makeba's services!

Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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4. E K.

Rover 101
Star Sitter
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
245 reviews
106 repeat clients
from
$45
per night

The best dog sitter on Rover! She always takes such good care of our dog and is so great at communicating, updating and sending photos. She’s always so flexible with pickup/drop-off and is so quick at respond to booking inquiries. We basically won’t leave our dog with anyone else and always check with Liz’s availability before booking travel because I don’t think our dog would want to stay anywhere else and we certainly wouldn’t want him to either.

Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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5. Ann-Marie H.

Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
2.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$50
per night

Ann-Marie took great care of my fur baby while I was out of town. She sent pictures throughout the stay, maintained communication, and was flexible when we pushed our return to a later time. I would definitely recommend her and look forward to hiring her again in the future.

Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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6. Ashley M.

Rover 101
Star Sitter
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
44 reviews
18 repeat clients
from
$52
per night

Really appreciate Ashley take care of our dog for a long weekend! Ashley is super considerate and communicative - you can expect to receive regular updates on how your pup is doing and you can tell she goes to great lengths to ensure every pet that stays with her has a great experience. I would absolutely choose Ashley again for boarding!

Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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7. Andrew T.

Star Sitter
WFH Couple, Park Nearby
Lower West Side, Chicago, IL, 60608
4.4 mi. away
Boarding
5.0 out of 5 stars
102 reviews
43 repeat clients
from
$45
per night

Andrew took great care of our four legged family member. Was very prompt in responding and excellent in providing us pictures to ease our worries. We would be happy to have Andrew take care of her again.

Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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8. Ebonee A.

Star Sitter
12 + years of Vet-Tech experience!
Hyde Park, Chicago, IL, 60615
2.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
30 reviews
14 repeat clients
from
$50
per night

Ebonee is absolutely amazing! Beautiful spirit, warm, and welcoming. My fur baby felt at home and probably has found his permanent sitter! Thanks for being an amazing 2nd home for Brownie! We’ll definitely see you again!

Sitter Profile Image: Gillian K.
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Sitter Profile Image: Gillian K.
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9. Gillian K.

Star Sitter
Loves long walks and fluffy friends
Bridgeport, Chicago, IL, 60608
3.3 mi. away
Boarding
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$40
per night

Our third time using Gillian’s pet sitting services and it was fantastic as usual! My dog is always so happy to come here, and Gillian does such a great job keeping us posted with silly photos. This time around my dog decided to hurt her paw days before my trip, but Gillian put my mind at ease with following her new medication routine and giving me updates on how her paw was doing.

Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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10. MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
2.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
13 reviews
2 repeat clients
from
$40
per night

Maria did a very good job taking care of Bubba while I was out of town. I would recommend Maria she not only cares for your pet, but also shows compassion towards their individual needs.

Sitter Profile Image: Jason M.
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Sitter Profile Image: Jason M.
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11. Jason M.

Experienced Professional
Lower West Side, Chicago, IL, 60608
3.6 mi. away
Boarding, Dog Walking
12 reviews
from
$50
per night

I am so very happy having Jason to care for my dog George. When I drive up to Jason’s Residence my dog is truly happy to see him Jason takes care of my dog and I trust him. He also make meals for my dog

Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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12. Willy J.

Reliable Dog Lover at your Service
Douglas, Chicago, IL, 60653
1.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$45
per night

Very accommodating, even for a last minute request. Kept me updated on things that could be of concern (my girl refused to eat because she’s dramatic) and sent pics/videos throughout the stay! Would recommend. Thank you again

Sitter Profile Image: Regan D.
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Sitter Profile Image: Regan D.
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13. Regan D.

Star Sitter
Your friendly neighborhood pet girl
Near North Side, Chicago, IL, 60654
4.9 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
34 reviews
14 repeat clients
from
$45
per night

Amazing care!! Couldn’t recommend Regan and Adam more. I’ll definitely be using them again. Daily photos, accommodating pick up/drop off and great people.

Sitter Profile Image: Briana V.
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Sitter Profile Image: Briana V.
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14. Briana V.

Star Sitter
Always home, 24/7 attention & care!
South Lawndale, Chicago, IL, 60623
5.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
46 reviews
12 repeat clients
from
$48
per night

Thank you Briana for making Blanca feel at home away from home. She made sure I knew my girl was ok and happy. I highly recommend her and I’ll be using her fing forward.

Sitter Profile Image: Melanie S.
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Sitter Profile Image: Melanie S.
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15. Melanie S.

Experienced Dog Owner and Dog Lover
Near North Side, Chicago, IL, 60654
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
157 reviews
62 repeat clients
from
$55
per night

Melanie was absolutely amazing with our dog. She provided daily updates of their adventures together, and made sure our dog was always entertained! I would highly recommend Melanie to anyone.

Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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16. Rachel W.

Star Sitter
Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
2.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
41 reviews
16 repeat clients
from
$65
per night

Our dog had a great time! We got lots of pictures and updates. They live close to a dog park and he got a lot of exercise. Flexible and friendly.

Sitter Profile Image: Dion F.
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Sitter Profile Image: Dion F.
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17. Dion F.

Your baby’s favorite hotel 🐕🦴
Near West Side, Chicago, IL, 60661
4.5 mi. away
Boarding
5.0 out of 5 stars
6 reviews
from
$50
per night

It’s always a little nerve wracking when you’re away from your pup for an extended period, but Dion was great with Brix! He was patient, kind, communicative and gave him plenty of long walks which we appreciate. Will be utilizing Dion in the future when needed :)

Sitter Profile Image: Georgia M.
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Sitter Profile Image: Georgia M.
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18. Georgia M.

Love to pet sit and going for walks
Near North Side, Chicago, IL, 60610
5.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$35
per night

Georgia was great! She was flexible, able to accommodate a last minute request and was very communicative. She sent some cute pictures of my pup and I could tell she had a good time! Would definitely feel great having her watch my pup again. Thanks Georgia!

Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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19. Katie M.

Star Sitter
Long time animal lover
Near North Side, Chicago, IL, 60610
5.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
160 reviews
55 repeat clients
from
$45
per night

Katie was so sweet and took great care of my dog who stayed with her for Thanksgiving week! I very much appreciated the daily picture updates!❤️

Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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20. Viola R.

Star Sitter
A dogs best friend
Hyde Park, Chicago, IL, 60615
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$30
per night

Viola did a fantastic job on taking care of my Zoë. She sent updates and pictures of everything that she had been doing for Zoë. I saw how comfortable she made Zoë feel being in her care. I will definitely have Viola to take care of Zoë again whenever Viola is available.

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Rover also offers other services in Oakland:

Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 7915 owners have reviewed sitters in Oakland, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect dog sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average dog boarding rates to get an idea before you start a conversation with a dog sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Oakland dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Oakland, Chicago, IL who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Oakland.

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